# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/376 data_Murph3_C18H18O2N2S2 _audit_creation_date 'Mon Aug 2 12:18:38 1999' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? _publ_requested_journal 'J. Chem. Soc. Perkin Trans. I' _publ_requested_coeditor_name ? _publ_contact_author_phone ' 0141 548 4241 ' _publ_contact_author_fax ' 0141 552 0876 ' _publ_contact_author_email ' a.r.kennedy@ccsun.strath.ac.uk ' loop_ _publ_author_name _publ_author_address ' FIRST AUTHORS NAME ' ; Dept. of P & A Chemistry University of Strathclyde 295 Cathedral St Glasgow G1 1XL Scotland ; _publ_section_title ; Diazadithiafulvalenes as Reactive Electron Donors ; #----------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan' _computing_structure_solution 'Sir' _computing_structure_refinement 'teXsan' _computing_publication_material 'teXsan' #----------------------------------------------------------------------- _cell_length_a 11.4859(8) _cell_length_b 9.025(1) _cell_length_c 16.407(1) _cell_angle_alpha 90 _cell_angle_beta 96.647(6) _cell_angle_gamma 90 _cell_volume 1689.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 21 _cell_measurement_theta_min 13.8 _cell_measurement_theta_max 19.0 #----------------------------------------------------------------------- _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' #----------------------------------------------------------------------- _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_meas 0.000 _chemical_formula_weight 358.47 _chemical_formula_analytical ? _chemical_formula_sum 'C18 H18 N2 O2 S2 ' _chemical_formula_moiety 'C18 H18 N2 O2 S2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 752.00 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type none #----------------------------------------------------------------------- _diffrn_special_details none _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector ? _diffrn_measurement_device 'Rigaku AFC7S diffractometer' _diffrn_measurement_method 'omega/2-theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 13.03 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 4327 _reflns_number_total 4128 _reflns_number_observed 2344 _reflns_observed_criterion 'I>2\s(I)' _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_reduction_process ? _diffrn_orient_matrix_UB_11 0.04246 _diffrn_orient_matrix_UB_12 0.07854 _diffrn_orient_matrix_UB_13 -0.02781 _diffrn_orient_matrix_UB_21 0.05643 _diffrn_orient_matrix_UB_22 0.01200 _diffrn_orient_matrix_UB_23 0.05075 _diffrn_orient_matrix_UB_31 0.05193 _diffrn_orient_matrix_UB_32 -0.07722 _diffrn_orient_matrix_UB_33 -0.02042 #----------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 72 0.003 0.002 'International Tables' H 0 72 0.000 0.000 'International Tables' N 0 8 0.006 0.003 'International Tables' O 0 8 0.011 0.006 'International Tables' S 0 8 0.125 0.123 'International Tables' #----------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom S(1) 0.80051(9) 0.4311(1) 0.29839(6) 0.0296 Uij ? ? S(2) 0.67980(9) 0.5090(1) 0.37156(6) 0.0281 Uij ? ? O(1) 0.6806(2) -0.0120(3) 0.3905(2) 0.0304 Uij ? ? O(2) 0.8264(2) 0.1550(3) 0.5468(2) 0.0318 Uij ? ? N(1) 0.8439(3) 0.1147(3) 0.3671(2) 0.0237 Uij ? ? N(2) 0.6519(3) 0.2552(3) 0.4946(2) 0.0231 Uij ? ? C(1) 0.9207(3) 0.3698(4) 0.3682(2) 0.0241 Uij ? ? C(2) 1.0100(4) 0.4702(4) 0.3944(2) 0.0302 Uij ? ? C(3) 1.1094(3) 0.4240(5) 0.4423(2) 0.0314 Uij ? ? C(4) 1.1237(3) 0.2754(5) 0.4634(2) 0.0319 Uij ? ? C(5) 1.0364(3) 0.1744(4) 0.4382(2) 0.0269 Uij ? ? C(6) 0.9341(3) 0.2211(4) 0.3923(2) 0.0228 Uij ? ? C(7) 0.8544(3) 0.0284(4) 0.2916(2) 0.0264 Uij ? ? C(8) 0.9132(3) -0.1217(5) 0.3094(2) 0.0327 Uij ? ? C(9) 0.7530(3) 0.0845(4) 0.4096(2) 0.0210 Uij ? ? C(10) 0.7484(3) 0.1714(4) 0.4899(2) 0.0222 Uij ? ? C(11) 0.6388(3) 0.3317(4) 0.5724(2) 0.0253 Uij ? ? C(12) 0.5722(4) 0.2417(4) 0.6293(2) 0.0329 Uij ? ? C(13) 0.5599(3) 0.2685(4) 0.4277(2) 0.0231 Uij ? ? C(14) 0.4620(3) 0.1784(4) 0.4264(2) 0.0288 Uij ? ? C(15) 0.3729(3) 0.1868(5) 0.3613(3) 0.0332 Uij ? ? C(16) 0.3825(4) 0.2858(4) 0.2979(2) 0.0338 Uij ? ? C(17) 0.4771(3) 0.3805(4) 0.3008(2) 0.0290 Uij ? ? C(18) 0.5659(3) 0.3729(4) 0.3660(2) 0.0230 Uij ? ? H(1) 0.9992 0.5643 0.3778 0.04(1) Uij ? ? H(2) 1.1716 0.4937 0.4616 0.03(1) Uij ? ? H(3) 1.1917 0.2431 0.4927 0.03(1) Uij ? ? H(4) 1.0452 0.0747 0.4512 0.025(10) Uij ? ? H(5) 0.9051 0.0818 0.2601 0.019(9) Uij ? ? H(6) 0.7720 0.0239 0.2631 0.022(9) Uij ? ? H(7) 0.9995 -0.1112 0.3333 0.05(1) Uij ? ? H(8) 0.8651 -0.1743 0.3455 0.04(1) Uij ? ? H(9) 0.9173 -0.1754 0.2602 0.022(9) Uij ? ? H(10) 0.7199 0.3609 0.5997 0.04(1) Uij ? ? H(11) 0.5916 0.4220 0.5603 0.014(8) Uij ? ? H(12) 0.6133 0.1465 0.6408 0.04(1) Uij ? ? H(13) 0.5686 0.2898 0.6797 0.05(1) Uij ? ? H(14) 0.4844 0.2214 0.6035 0.06(1) Uij ? ? H(15) 0.4540 0.1092 0.4702 0.03(1) Uij ? ? H(16) 0.3112 0.1261 0.3632 0.021(9) Uij ? ? H(17) 0.3258 0.2851 0.2497 0.025(10) Uij ? ? H(18) 0.4844 0.4554 0.2562 0.03(1) Uij ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0353(5) 0.0319(5) 0.0220(4) 0.0047(4) 0.0043(4) 0.0069(4) S(2) 0.0350(5) 0.0203(5) 0.0291(5) 0.0043(4) 0.0041(4) 0.0023(4) O(1) 0.032(1) 0.022(1) 0.037(1) -0.007(1) 0.005(1) -0.007(1) O(2) 0.031(1) 0.038(2) 0.025(1) 0.007(1) -0.003(1) -0.001(1) N(1) 0.030(2) 0.021(1) 0.020(1) -0.003(1) 0.003(1) -0.003(1) N(2) 0.026(2) 0.022(1) 0.020(1) 0.002(1) 0.001(1) -0.003(1) C(1) 0.029(2) 0.025(2) 0.019(2) 0.001(2) 0.004(1) -0.001(1) C(2) 0.046(2) 0.022(2) 0.025(2) -0.005(2) 0.012(2) -0.002(1) C(3) 0.036(2) 0.034(2) 0.026(2) -0.011(2) 0.008(2) -0.004(2) C(4) 0.026(2) 0.043(2) 0.026(2) 0.001(2) 0.000(2) -0.006(2) C(5) 0.029(2) 0.025(2) 0.026(2) 0.001(2) 0.003(2) 0.002(2) C(6) 0.028(2) 0.022(2) 0.019(2) -0.004(2) 0.006(1) -0.002(1) C(7) 0.025(2) 0.030(2) 0.025(2) -0.004(2) 0.005(1) -0.002(2) C(8) 0.031(2) 0.033(2) 0.034(2) 0.006(2) 0.005(2) -0.010(2) C(9) 0.020(2) 0.019(2) 0.023(2) 0.004(1) 0.002(1) 0.002(1) C(10) 0.026(2) 0.018(2) 0.022(2) -0.001(1) 0.002(1) 0.001(1) C(11) 0.035(2) 0.020(2) 0.021(2) 0.002(2) 0.002(2) -0.002(1) C(12) 0.042(2) 0.028(2) 0.030(2) 0.002(2) 0.011(2) 0.002(2) C(13) 0.024(2) 0.021(2) 0.023(2) 0.006(2) 0.000(1) -0.002(1) C(14) 0.032(2) 0.022(2) 0.032(2) 0.003(2) 0.001(2) -0.001(2) C(15) 0.020(2) 0.032(2) 0.047(2) 0.002(2) 0.000(2) -0.011(2) C(16) 0.035(2) 0.035(2) 0.028(2) 0.016(2) -0.010(2) -0.013(2) C(17) 0.033(2) 0.029(2) 0.024(2) 0.012(2) -0.003(2) -0.005(2) C(18) 0.019(2) 0.024(2) 0.027(2) 0.004(1) 0.002(1) -0.003(1) #----------------------------------------------------------------------- _refine_special_details ; H atoms were position from difference synthesise - only their isotropic temperature factors were refined. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '1/\s^2^(F)' _refine_ls_hydrogen_treatment 'refine Biso' _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_extinction_coef '5.9(17)x10^-7^' _refine_ls_number_reflns 2344 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_obs 0.0471 _refine_ls_R_factor_all 0.1221 _refine_ls_wR_factor_obs 0.0570 _refine_ls_wR_factor_all 0.0653 _refine_ls_goodness_of_fit_obs 1.570 _refine_ls_shift/esd_max 0.0001 _refine_ls_shift/esd_mean ? _refine_diff_density_min -0.51 _refine_diff_density_max 0.53 #----------------------------------------------------------------------- _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S(1) S(2) 2.060(1) ? ? yes S(1) C(1) 1.777(4) ? ? yes S(2) C(18) 1.789(4) ? ? yes O(1) C(9) 1.220(4) ? ? yes O(2) C(10) 1.227(4) ? ? yes N(1) C(6) 1.438(4) ? ? yes N(1) C(7) 1.480(4) ? ? yes N(1) C(9) 1.349(4) ? ? yes N(2) C(10) 1.351(4) ? ? yes N(2) C(11) 1.474(4) ? ? yes N(2) C(13) 1.438(4) ? ? yes C(1) C(2) 1.399(5) ? ? yes C(1) C(6) 1.402(5) ? ? yes C(2) C(3) 1.374(6) ? ? yes C(2) H(1) 0.896(4) ? ? no C(3) C(4) 1.390(6) ? ? yes C(3) H(2) 0.977(4) ? ? no C(4) C(5) 1.382(5) ? ? yes C(4) H(3) 0.916(4) ? ? no C(5) C(6) 1.386(5) ? ? yes C(5) H(4) 0.927(4) ? ? no C(7) C(8) 1.527(5) ? ? yes C(7) H(5) 0.953(4) ? ? no C(7) H(6) 1.007(4) ? ? no C(8) H(7) 1.028(4) ? ? no C(8) H(8) 0.979(4) ? ? no C(8) H(9) 0.947(4) ? ? no C(9) C(10) 1.539(5) ? ? yes C(11) C(12) 1.510(5) ? ? yes C(11) H(10) 1.021(4) ? ? no C(11) H(11) 0.986(4) ? ? no C(12) H(12) 0.988(4) ? ? no C(12) H(13) 0.940(4) ? ? no C(12) H(14) 1.063(4) ? ? no C(13) C(14) 1.386(5) ? ? yes C(13) C(18) 1.391(5) ? ? yes C(14) C(15) 1.393(5) ? ? yes C(14) H(15) 0.965(4) ? ? no C(15) C(16) 1.386(6) ? ? yes C(15) H(16) 0.899(4) ? ? no C(16) C(17) 1.379(6) ? ? yes C(16) H(17) 0.963(4) ? ? no C(17) C(18) 1.392(5) ? ? yes C(17) H(18) 1.007(4) ? ? no #----------------------------------------------------------------------- loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S(2) S(1) C(1) 104.8(1) ? ? ? yes S(1) S(2) C(18) 105.9(1) ? ? ? yes C(6) N(1) C(7) 117.8(3) ? ? ? yes C(6) N(1) C(9) 124.1(3) ? ? ? yes C(7) N(1) C(9) 118.0(3) ? ? ? yes C(10) N(2) C(11) 118.6(3) ? ? ? yes C(10) N(2) C(13) 122.5(3) ? ? ? yes C(11) N(2) C(13) 118.8(3) ? ? ? yes S(1) C(1) C(2) 118.9(3) ? ? ? yes S(1) C(1) C(6) 122.1(3) ? ? ? yes C(2) C(1) C(6) 118.8(3) ? ? ? yes C(1) C(2) C(3) 120.7(3) ? ? ? yes C(2) C(3) C(4) 120.1(4) ? ? ? yes C(3) C(4) C(5) 120.1(4) ? ? ? yes C(4) C(5) C(6) 120.1(4) ? ? ? yes N(1) C(6) C(1) 120.4(3) ? ? ? yes N(1) C(6) C(5) 119.3(3) ? ? ? yes C(1) C(6) C(5) 120.2(3) ? ? ? yes N(1) C(7) C(8) 112.6(3) ? ? ? yes O(1) C(9) N(1) 123.8(3) ? ? ? yes O(1) C(9) C(10) 119.6(3) ? ? ? yes N(1) C(9) C(10) 116.4(3) ? ? ? yes O(2) C(10) N(2) 123.7(3) ? ? ? yes O(2) C(10) C(9) 119.7(3) ? ? ? yes N(2) C(10) C(9) 116.4(3) ? ? ? yes N(2) C(11) C(12) 113.1(3) ? ? ? yes N(2) C(13) C(14) 119.1(3) ? ? ? yes N(2) C(13) C(18) 121.2(3) ? ? ? yes C(14) C(13) C(18) 119.7(3) ? ? ? yes C(13) C(14) C(15) 120.2(4) ? ? ? yes C(14) C(15) C(16) 119.7(4) ? ? ? yes C(15) C(16) C(17) 120.3(4) ? ? ? yes C(16) C(17) C(18) 120.0(4) ? ? ? yes S(2) C(18) C(13) 121.7(3) ? ? ? yes S(2) C(18) C(17) 118.1(3) ? ? ? yes C(13) C(18) C(17) 119.9(3) ? ? ? yes #----------------------------------------------------------------------- #----------------------------------------------------------------------- #===END